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Abstract:

Satisfactory procedures are described for the synthesis of 5,6- and 3,4-thiirane derivatives from the respective hexofuranose or hexopyranose epoxide precursors. The controlled ring-opening reaction of thiiranes by 1-thioaldoses was successfully accomplished to afford, regio- and stereoselectively, β-S-(1→4)-3,4-dithiodisaccharides. For instance, the regioselective attack of per-O-acetyl-1-thioglucose (16) to C-4 of 2-propyl 2,6-di-O-acetyl-3,4-epithio-α-d-galactopyranoside (14) gave the derivative of Glcp-β-S-(1→4)-3,4-dithioGlcp-O-iPr (17). This thiodisaccharide was accompanied by the (1→3)-disulfide 18, formed between 16 and 17, and the symmetric (3→3)-disulfide 19, which resulted from the oxidative dimerization of 17. However, the S-acetyl derivative of 17 could be obtained in good yield (62%) by LiAlH 4 reduction of the crude mixture 17-19, followed by acetylation. The same sequence of reactions starting from 14 and the 1-thiolate of Galp afforded the per-O,S-acetyl derivative of Galp-β-S-(1→4)-3,4-dithio-α-d-Glcp-O-iPr (23), which was selectively S-deacetylated to give 25. The dithiosaccharides 17 and 25 are 3,4-di-S-analogues of derivatives of the natural disaccharides cellobiose and lactose, respectively. The ring-opening reaction of 5,6-epithiohexofuranoses of d-galacto (8) or l-altro (11) configuration with 1-thioaldoses was also regio- and stereoselective to give the respective β-S-(1→6)-linked 5,6-dithiodisaccharides 26 or 29 in excellent yields. Glycosylation of the free thiol group of 17, 25, or 26, using trichloroacetimidates as glycosyl donors, led to the corresponding branched dithiotrisaccharides. Some of them are sulfur analogues of derivatives of branched trisaccharides found in natural polysaccharides. © 2011 American Chemical Society.

Registro:

Documento: Artículo
Título:Synthesis of branched dithiotrisaccharides via ring-opening reaction of sugar thiiranes
Autor:Repetto, E.; Manzano, V.E.; Uhrig, M.L.; Varela, O.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Argentina
Palabras clave:Cellobiose; Crude mixtures; Free thiol group; Glycosyl donors; Good yield; Natural polysaccharide; Oxidative dimerization; Regio-selective; Ring opening reaction; Stereo-selective; Sulfur analogues; Thiiranes; Trichloroacetimidates; Acetylation; Sugars; Sulfur; Synthesis (chemical); 3,4 thiirane derivative; 5,6 thiirane derivative; carbohydrate derivative; cellobiose; dithiotrisaccharide; lactose; trichloroacetimidic acid; unclassified drug; acetylation; article; deacetylation; dimerization; glycosylation; ring opening; stereochemistry; synthesis; Carbohydrate Conformation; Carbohydrate Sequence; Disaccharides; Glucose; Glycosylation; Stereoisomerism; Sulfides; Trisaccharides
Año:2012
Volumen:77
Número:1
Página de inicio:253
Página de fin:265
DOI: http://dx.doi.org/10.1021/jo2018685
Título revista:Journal of Organic Chemistry
Título revista abreviado:J. Org. Chem.
ISSN:00223263
CODEN:JOCEA
CAS:cellobiose, 16462-44-5, 528-50-7; lactose, 10039-26-6, 16984-38-6, 63-42-3, 64044-51-5; 1-thioglucose, 7534-35-2; Disaccharides; Glucose, 50-99-7; Sulfides; Trisaccharides; ethylene sulfide, 420-12-2
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v77_n1_p253_Repetto

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Citas:

---------- APA ----------
Repetto, E., Manzano, V.E., Uhrig, M.L. & Varela, O. (2012) . Synthesis of branched dithiotrisaccharides via ring-opening reaction of sugar thiiranes. Journal of Organic Chemistry, 77(1), 253-265.
http://dx.doi.org/10.1021/jo2018685
---------- CHICAGO ----------
Repetto, E., Manzano, V.E., Uhrig, M.L., Varela, O. "Synthesis of branched dithiotrisaccharides via ring-opening reaction of sugar thiiranes" . Journal of Organic Chemistry 77, no. 1 (2012) : 253-265.
http://dx.doi.org/10.1021/jo2018685
---------- MLA ----------
Repetto, E., Manzano, V.E., Uhrig, M.L., Varela, O. "Synthesis of branched dithiotrisaccharides via ring-opening reaction of sugar thiiranes" . Journal of Organic Chemistry, vol. 77, no. 1, 2012, pp. 253-265.
http://dx.doi.org/10.1021/jo2018685
---------- VANCOUVER ----------
Repetto, E., Manzano, V.E., Uhrig, M.L., Varela, O. Synthesis of branched dithiotrisaccharides via ring-opening reaction of sugar thiiranes. J. Org. Chem. 2012;77(1):253-265.
http://dx.doi.org/10.1021/jo2018685